C11: Alcohol Reactions

Question 1

oxidation of alkane to carboxylic acid

Answer 1

alkane – 1 alcohol – aldehyde – carboxylic acid

Question 2

oxidation of alkane to ketone

Answer 2

alkane – 2ndary alcohol – ketone

Question 3

R-OH –_____–> alkenes

Answer 3

dehydration

Question 4

R-OH –_____–> ketones, aldhydes, acids

Answer 4

oxidation

Question 5

R-OH –_____–> R-X (halides)

Answer 5

substitution

Question 6

R-OH –_____–> R-H (alkanes)

Answer 6

reduction

Question 7

R-OH –_____–> R-O-C(=O)-R’ (esters)

Answer 7

esterification

Question 8

R-OH –_____–> R-OTs (tosylate esters)

Answer 8

tosylation

Question 9

R-OH –______–>–______–> R-O-R’ (ethers)

Answer 9

[1] form alkoxide [2] R’X

Question 10

___ and ____ ____ are easily oxided

Answer 10

Primary, Secondary, Alcohols

Question 11

oxidation of ____ alcohols gives ketones

Answer 11

secondary

Question 12

oxidation of ____ alcohols gives aldehydes

Answer 12

primary

Question 13

______ can be further oxidized to carboxylic acid

Answer 13

aldhydes

Question 14

Primary alcohol + ______ = carboxylic acid

Answer 14

Chromic acid

HO-(O=)Cr(=O)-OH

Question 15

Primary alcohol + ______ = stop at aldehyde

Answer 15

PCC. HCl. (Pyridine or dichloromethane)

Question 16

Collins Reagent

Answer 16

Chromium Trioxide + Pyridine

CrO3 + (benzene ring with N replacing one carbon)

Question 17

Jones Reagent

Answer 17

Chromic acid + Hydrosulfuric acid + acetone

CrO3 + H2SO4 + CH3-C(=O)-CH3

Question 18

Bleach

Answer 18

Sodium hypochlorite

NaOCl

Question 19

DMSO4, Swerns Reagent

Answer 19

dimethyl sulfoxide, oxalyl chloride and triethyl amine

CH3-(S=O)C-CH3 , (COCl)2

Question 20

Secondary Alcohol oxidized to ketone by

Answer 20

Chromium Reagent: Chromic acid or PCC

Non Chromium Reagent: Bleach, Swern, DMP

Question 21

Primary Alcohol oxidized to aldehyde by

Answer 21

Chromium Reagent: PCC

Non Chromium Reagent: Swern or DMP

Question 22

Primary Alcohol oxidized to carboxylic acid by

Answer 22

Chromium Reagent: Chromic acid

Non Chromium Reagent: Bleach

Question 23

R-OH + TsOH

alcohol + p-toluenesulfonic acid

Answer 23

R-O-Ts + H20
alkyl tosylate (p-toluenesulfonate ester) + water

Question 24

Primary alcohol + TsCl/pyridine –______—>

Answer 24

nucleophile: - (substitution, OH replaced by nucleophile)
base: - (elimination, C=C formed)

Question 25

____ displacement of tosylate ion, with inversion

Answer 25

SN2

Question 26

R-OTs + -OH ---> ????

Answer 26

R-OH + -OTs | alcohol

Question 27

R-OTs + -C(triplebond)N ---> ????

Answer 27

R-C(triplebond)N + -OTs | nitrile

Question 28

R-OTs + Br- ---> ????

Answer 28

R-Br + -OTs | alkyl halide

Question 29

R-OTs + R'-O- ---> ????

Answer 29

R-O-R' + OTs | ether

Question 30

R-OTs + :NH3 ---> ????

Answer 30

R-NH3+/-OTs | amine salt

Question 31

R-OTs + LiAlH4, LAH ---> ????

Answer 31

R-H + -OTs | alkane

Question 32

Tertiary alcohol + HBr --____--> ????

Answer 32

SN1, carbocation formed

Question 33

Primary alcohol + HBr --____--> ????

Answer 33

SN2, no carbocation formed

Question 34

HCl + ZnCl2 , does what

Answer 34

Lucas Reagent, replaces OH

Question 35

___ and ____ alcohols react with Lucas reagent by SN1, a _____ reaction

Answer 35

secondary, tertiary, fast

Question 36

___ and ____ alcohols react with Lucas reagent by SN2, a _____ reaction

Answer 36

methyl and primary, slow

Question 37

Order of reactivity of alcohols with sulfuric acid

Answer 37

3>2>1

Question 38

Chromic acid test distinguishes ____ from ____ by ____

Answer 38

tertiary from secondary and primary by color, tertiary stays orange, secondary and primary turn blue green

Question 39

Lucas test distinguishes ___ from ___ by ____

Answer 39

Primary from secondary from tertiary by reaction rate Primary - takes forever Secondary - takes 1-5 min Tertiary - takes less than a minute

Question 40

Best reagents for converting primary alcohol to alkyl halide

Answer 40

Chloride: SOCl2 Bromide: PBr3 or HBr Iodide: I2

Question 41

Best reagents for converting secondary alcohol to alkyl halide

Answer 41

Chloride: SOCl2 Bromide: PBr3 Iodide: I2

Question 42

Best reagents for converting tertiary alcohol to alkyl halide

Answer 42

Chloride: HCl Bromide: HBr Iodide: HI

Question 43

acid dehydration of alcohol mechanism, works best with ____, follows _______ rule stating that the _____ substituted alkene will form

Answer 43

E1, tertiary and secondary, rearrangement may occur, Zaitsev rule, most

Question 44

H3C-H2C-OH ---______---> CH2=CH2

Answer 44

H2SO4, heat

Question 45

H3C-H2C-OH ---______---> H3C-H2C-O-CH2- _

Answer 45

H2SO4, no heat

Question 46

_____ migration after carbocation formation of a _____ forms a _____

Answer 46

methyl , pinacol, pinacolone

Question 47

alkene ---______---> glycol ----______---> ketones and aldhydes

Answer 47

[1] OsO4/H202 [2] HIO4

Question 48

alcohol + nitric acid | R-OH + H-O-N(=O)-O-

Answer 48

alkyl nitrate ester + water | R-O-N(=O)-O-

Question 49

phosphoric acid + alcohol (up to x3)

Answer 49

[1] mono-R-phosphate [2] di-R-phosphate [3] tri-R-phosphate

Question 50

Williamson Ether Synthesis (step 1)

Answer 50

Alcohol + Na(NaH or K) ---> R-O- +Na + H2

Question 51

Williamson Ether Synthesis (step 2)

Answer 51

alkoxide displaces the leaving group of a good SN2 substrate | R-O- + R'-CH2-X ---> R-O-CH2-R' + XNa